Getting from A to B (aka The Big Wrap Up): Route 66

A large part of our early dating days were dominated by curious conversations; we’d daydream about where we might live one day, what cities we wanted to explore together and how many pets is too many pets? We’re still figuring out the answer to that last one, but one thing we knew for sure was that we wanted to take road trips together, city hop and have little to no agenda. The ‘no agenda’ part of the equation isn’t always possible, but as we’ve found a way to force our wanderlust tendencies into reality, we’ve worked out and reined in unwelcome kinks on our road-tripping adventures – from the California Coast to the Pacific Northwest, and most recently, our cross country drive down Route 66.


When we hunkered down and became serious about nailing down the dates of our Route 66 trip, we had a difficult time finding any information on the best way to do so. Do we rent a car one way? Do we drive our car both ways? Do we buy a used car and sell it when we get to Los Angeles? As we began planning, it became clear that there was no right or wrong answer, but as we stumbled upon 66 forums and travel diaries, the logistics of making this 2,500+ mile trip felt confusing and, to be honest, somewhat dated. Because we wished we could have found a more helpful resource, we wanted to share how we got from Point A to Point B, in the hopes that it would encourage or inspire at least one person to embark on a similar journey! We came home exhausted, yes, but also recharged and brimming with ideas (maybe too much so? I’m exhausted all over again!). In any case, getting outside of our comfort zone is always energizing, and this trip reminded us of that.

SCHEDULING. Between our collective work schedules, we knew that there was only a two week window – max! – in which to make this work. With those weeks sandwiched between weekends and choosing to begin over Labor Day ensured that Scott would only need to request 9 days off of work, but it would still allow us a full 16 days of adventure! We printed a September calendar and began penciling in which days we’d hope to be in which city, and we simply Googled the drive times between each to make sure it was feasible. We overestimated the time frames as we’d be nixing main highways as much as possible, and we knew that to see everything we wanted, we’d need to drive one way and fly back in the end.

MONEY SAVERS. We realized that by signing up with AAA, we’d be able to save hundreds of dollars on a one-way cross country car rental. Although the car was still the largest expense, we enjoyed ‘Skeeter’ (lovingly dubbed by Scott), our little Mazda 2. In some cases, mentioning AAA while checking into hotels lowered nightly rates, and by the end of the trip, our membership paid for itself ten-fold (twenty-fold, maybe?). We didn’t pre-book our hotels (with the exception of The Saguaro in Palm Springs), but if you’re comfortable enough to wing it, we also found great rates by comparison shopping between these money saving apps as we arrived in each new city: Hotel Tonight, and of course, Priceline and Trip Advisor.


PACKING. When it came time to pack, we had to remind ourselves that we’d be flying back home – and no one hates checking a bag more than we do. (The wait! The crushed souvenirs! The exploding shampoo!) We each had one small carry-on suitcase and a backpack each – our Bellbrook bag for Scott and our tiny Baggu for me. We’ve already had friends and readers reach out with questions on our packing priorities (which is simultaneously funny and sweet), so for those interested, here’s what we did:

  • While the Bellbrook contained our camera gear and laptop, the Baggu held our smaller items: car phone chargers, headphones (for the flight home), a mobile hotspot, an e-reader and travel sized toiletries.
  • We knew we’d only need 2 weeks worth of toothpaste, hair goos and the like, and so we spent less than $10 on travel-sized products that we’d be able to toss before boarding the plane.
  • We didn’t pack fancy. Aside from one tank dress and pair of heels (for good measure; I can’t speak for Scott, you know?), we stuck to tees, a single pair of jeans and a couple of shorts. Because we stayed with my cousin in Oklahoma City, we washed one small load less than a week in, but all in all, we had 10 days worth of clothes. Some items didn’t get worn at all!
  • We filled one grocery-sized bag with road snacks, knowing that whatever didn’t get consumed could stay with our friend, Kalli, in Los Angeles. Of course we packed wine for me and gin for Scott, so we could always end our day with a night cap!
  • If during our adventure we found something that needed to come home with us, we promised each other that – unless it was, say, a marble table or something equally large and heavy (which, of course, happened too many times to count) – we would buy it. We did end up with a handful of vintage books, bags of coffee and a new throw blanket, but we stuffed it all in a shipping box on our last day in LA, and we mailed it home.

STAYING (LITERALLY) ON TRACK. Route 66 was replaced in some areas by main thoroughfares, but often times, a frontage road would run parallel. The route winds in and out of towns – large and small – between Chicago and Los Angeles, and in most cases, these roads are unmarked. To make sure we stayed on track, we downloaded the Road Trip 66 app, and we could not have done the trip without it! While there are some improvements that could be made to the app itself, as long as you stayed on the red line, you were on 66. There have been a handful of alignments to the route over the last several decades, but every option was given while also marking roadside attractions along the way:


We also picked up the EZ66 Guide For Travelers, which while being extremely thorough, was an amusing read! The author of the book is clearly passionate about Route 66, and in reading the page-by-page play-by-play, you could really get a feel for his personality. At one point, he went so far as to give out his home’s cross streets in Oklahoma. In his words: I work at home, so visitors are welcome anytime! This is followed by his cell phone number, which is so endearing, I almost can’t even. Although there was a bit of a learning curve to the book, once we got the hang of it, it made a great companion to the Road Trip 66 app.


ENTERTAINMENT. We logged almost 60 hours of car time, between stopping on a whim, driving late into the evenings and making sure we stayed on the most scenic of paths. Although we spent a surprising amount of time riding in silence and taking in the sights, we did make sure to load up on entertainment for all the in-betweens. For fun, we packed up a handful of our old unmarked college-day CDs and laughed as we listened to the music that had us cringing, laughing or saying, oh, man, this brings me BACK! In addition, we downloaded hours of podcasts, with some favorites being: WTF with Marc Maron, Girl on Guy, Here’s the Thing, Mortified and of course, The Lively Show by our dear friend Jess (miss you, girl!).

THE RULES… OR LACK OF RULES, REALLY. If one of us wanted to stop – whether it was to snap a photo, stretch our legs or grab a bite, we stopped. The whole idea behind this trip was to see and explore things we wouldn’t normally see or explore, and so, at some points, we’d be stopping every 30 minutes! Did this set us back at times? Absolutely! Was it worth it? Absolutely.


BY THE NUMBERS. Here’s how it all shook out:

 Miles driven = 2,767
 Days traveled = 16
 # of states visited = 8
 Gallons of gas = 90
 Average cost of gas/gallon = $2.69
 Shortest stretch in the car = 3 hours (Tulsa to OKC)
Longest stretch in the car = 10 hours (OKC to Santa Fe!)
 Photos taken = 1,350
 Coffees consumed = 2/day x 2 of us x 16 days = 64 (ouch)
 # of signs with our pets’ initials = 3 (CC + J + M)
 # of times we cheated and hopped on the highway = 2, er, 3 (Hunger was typically to blame.)

Once again, thank you for all of your suggestions along the way. We ate well, we saw beautiful things, and we had our fill of boozy goodness, and we owe some of our favorite stops to you. We sincerely hope you enjoyed following along (we loved having you!), and we encourage you to chime in with any of your own travel tips, too!

PS… See part I, part II and part III of our Route 66 journey!

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  • Kim10.2.15 - 9:02 AM

    I love hearing about your adventure! It truly seemed like the trip of a lifetime. My husband I went on a cross-country roadtrip for our honeymoon last summer and it was awesome. So many of your tips ring true for us too.

    One tip I’d mention for future trips is the app Roadtrippers! We used to plan our stops and driving distances each day and it was awesome! It won’t let me link to our honeymoon itinerary but you can see more here: Definitely recommend.ReplyCancel

    • Kim10.2.15 - 9:45 AM

      Shoot, wish we’d known about that one – great tip, thanks!

      And HOLY COW. How in the world did you do all that in 2 weeks?! Did you have time to stop and think for a day? Teach me your secrets.ReplyCancel

  • Sarah @ onesuchlife10.2.15 - 10:32 AM

    What an adventure! You take beautiful pictures.ReplyCancel

  • Crystal10.2.15 - 10:32 AM

    So I want to know- did you stop by the book author’s place?ReplyCancel

    • Kim10.2.15 - 10:42 AM

      Haha, no, although we seriously considered it! But then we thought, how strange…ReplyCancel

  • Monika & Sam10.2.15 - 10:53 AM

    You guys do an amazing job with the planning of EVERYTHING; so I’m not surprised this was a terrific trip. Totally impressed and can’t wait to see what treasurers you brought back!ReplyCancel

  • Diana10.2.15 - 1:23 PM

    Loved this and all your earlier posts! I’ve recently decided I want to drive this some day too! Looks awesome!ReplyCancel

  • Kamille10.4.15 - 1:13 PM

    Not to be too nosy, but how about cost? It’s really hard to know how much a trip like this would cost. Would you be willing to break it down that way?ReplyCancel

    • Kim10.5.15 - 10:31 AM

      Hi Kamille!

      The largest cost was by far the one way car rental, which can definitely vary based on distance or current promotions, but we locked in a rate of $1300. The next largest cost was our hotel stays, but our flights home were less than $400 total. Luckily, gas was barely $250 for the entire drive!

      All that to say, we budgeted $4000 for everything (car, flight, hotels, gas, meals, entertainment), and we stuck to it! I should have mentioned this in the post, but starting last fall, we began an auto transfer to tuck $30/week into a vacation savings account (so we never even missed it), and when we could, we’d kick in more money – maybe $100 every couple of months. We paid for everything while we were gone on a cash back credit card, and I paid it off using the savings account when we returned!ReplyCancel

  • Josh | The Kentucky Gent10.5.15 - 12:52 PM

    Never realized AAA had car rental discounts, thanks for helping a brother out ;) and also for this cheat sheet. I need to get on this trip!

    Josh | The Kentucky Gent

    • Kim10.5.15 - 2:00 PM

      It was surprising how many ways AAA could save money! It never hurts to ask…ReplyCancel

  • Chanel10.5.15 - 1:28 PM

    You guys are truly inspirational! Great tips and your pictures def gives me wanderlust to visit parts of the US that normally wouldn’t be on the top of my list.

    My husband and I took a road trip to Louisville, Nashville, and Memphis last year and we didn’t kill each other…so naturally a longer road trip is in order ;) In a couple of weeks, we plan on taking a long weekend trip to do the Michigan mitten up to the UP.

    – cncReplyCancel

    • Kim10.5.15 - 1:59 PM

      Oh, how fun! Michigan will be so pretty at this time of year. :)ReplyCancel

  • Trude10.6.15 - 5:40 PM

    Thank you for sharing your tips! This kind of road trip really calls to me. Going up Highway 1 from the OC to San Francisco is still one of my favorite vacations of all time. :) My fiance and I have always wanted to do a road trip through the South, visiting Civil War sites – that may be our honeymoon! Love seeing everyone’s tips too!ReplyCancel

  • […] it happens to be one of the things I enjoy most. Why does travel have to be so dang expensive?! Kim and Scott’s Route 66 trip has me seriously ready to empty the bank account though. Who’s with […]ReplyCancel

  • […] September, Scott and I took a two-week road trip across America, hugging Route 66 from Chicago to Los Angeles! It was an experience of a lifetime – exhilarating, […]ReplyCancel


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